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Despite the very large literature on teacher careers from an individual perspective, there is relatively little that links the perspectives of teachers themselves to how schools as organisations approach careers. The aim of this paper is, first, to outline how teachers’ orientations towards careers change across three dimensions, and, second, to examine how schools as organisations deal with career, developing a model of organisational responses, including developing a concept of ‘career culture’, derived from an analysis of interviews regarding the first three years of teaching conducted with senior leaders and second-year teachers themselves. By considering the fit between individuals’ career orientations and school career cultures, the paper surfaces both the fluid nature of these orientations and the subsequent potential instability of the fit.